Identification of the Sex Pheromone of a Protected Species, the Spanish Moon Moth Graellsia isabellae

Journal of Chemical Ecology

Volumn 36, Issue 9, 2010, Pages 923-932

  Millar, Jocelyn G ^a   McElfresh, J Steven ^a   Romero, Carmen ^a   Vila, Marta ^b   Marí Mena, Neus ^b   Lopez Vaamonde, Carlos ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF A CORUÑA   (Spain)

^c Inst Natl de la Rech Agronom   (France)

Author keywords

(4E,6E,11Z) hexadecatrienal; Graellsia isabellae; Lepidoptera; Pheromone; Protected species; Saturniidae

Indexed keywords

SEX PHEROMONE;

BIOCONTROL AGENT; BIOGEOCHEMISTRY; ENDANGERED SPECIES; FIELDWORK; MOTH; PHEROMONE TRAP; SAMPLING; SEX PHEROMONE;

ANIMAL; ARTICLE; CHEMISTRY; DRUG EFFECT; ENVIRONMENTAL PROTECTION; FEMALE; GAS CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MALE; MOTH; SOLID PHASE MICROEXTRACTION;

ANIMALS; CHROMATOGRAPHY, GAS; CONSERVATION OF NATURAL RESOURCES; FEMALE; MALE; MOTHS; SEX ATTRACTANTS; SOLID PHASE MICROEXTRACTION;

FRANCE; SPAIN; SWITZERLAND;

GRAELLSIA ISABELLAE; HEXAPODA; LEPIDOPTERA; SATURNIIDAE;

EID: 77956871148     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-010-9831-1     Document Type: Article

References (29)

1. 2-catalyzed intramolecular [4 + 2] cycloaddition of tethered alkynyl and alkenyl enynones and enynals: a new synthetic method for functionalized polycyclic hydrocarbons. J. Org. Chem. 70: 3682-3685.
2. Bestmann, H. J., Attygalle, A. B., Brosche, T., Erler, J., Platz, H., Schwarz, J., Vostrowsky, O., Wu, C.-H., Kaissling, K. E., and Chen, T.-M. 1987. Identification of three sex pheromone components of the female Saturniid moth Antheraea pernyi (Lepidoptera: Saturniidae). Z. Naturforsch. C. 42: 631-636.
3. Bestmann, H. J., Attygalle, A. B., Schwarz, J., Garge, W., Vostrowsky, O., and Tomida, I. 1989. Pheromones 71. Identification and synthesis of female sex pheromone of Eri-silkworm, Samia cynthia ricini (Lepidoptera: Saturniidae). Tetrahedron Lett. 30: 2911-2914.
4. Buck, M. and Chong, J. M. 2001. Alkylation of 1-alkynes in THF. Tetrahedron Lett. 42: 5825-5827.
5. Chefaoui, R. M. and Lobo, J. M. 2007. Assessing the conservation status of an Iberian moth using pseudo-absences. J. Wildl. Manage. 71: 2507-2516.
6. Chefaoui, R. M. and Lobo, J. M. 2008. Assessing the effects of pseudo-absences on predictive distribution model performance. Ecol. Modell. 210: 478-486.
7. Collectif O. P. I. E. 1998. Contribution à la connaissance de Graellsia isabellae galliaegloria Oberthur (Lépidoptère, Attacidae), connu uniquement en France. Rapport d'Études de l'OPIE 3: 1-36. Office pour les Insectes et leur Environnement, Guyancourt, France.
8. Cossé, A. A., Bartelt, R. J., Zilkowski, B. W., Bean, D. W., and Petroski, R. J. 2005. The aggregation pheromone of Diorhabda elongata, a biological control agent of saltcedar (Tamarix spp.): identification of two behaviorally active components. J. Chem. Ecol. 31: 657-670.
9. Ducoux, J.-P., Le Ménez, P., Kunesch, N., Kunesch, G., and Wenkert, E. 1992. An efficent and stereoselective synthesis of insect pheromones by way of nickel-catalyzed Grignard reactions. Syntheses of gossyplure and pheromones of Eudia pavonia and Drosophila melanogaster. Tetrahedron 48: 6403-6412.
10. El-Sayed, A. 2009. The Pherobase. http://www. pherobase. com.
11. Ibáñez Gázquez, S., Nevado Ariza, J. C., and Ylla Ullastre, J. 2008. Graellsia isabelae (Graells, 1849), una nueva especie para la fauna lepidopterológica de Almería (España) (Lepidoptera: Saturniidae): SHILAP. Rev. Lepidopterol. 36: 427-430.
12. International Union for the Conservation of Nature. 2007. IUCN Red List of Threatened Species. URL http://www. iucnredlist. org.
13. Joshi, N. N., Mamdapur, V. R., and Chadha, M. S. 1984. Stereoselective and versatile approach for the synthesis of gossyplure and its components. Tetrahedron 40: 3285-9.
14. Kean, J. M. and Suckling, D. M. 2005. Estimating the probability of eradication of painted apple moth from Auckland. N. Z. Plant Protection 58: 7-11.
15. Kochansky, J., Tette, J., Taschenberg, E. F., Cardé, R. T., Kaissling, K.-E., and Roelofs, W. L. 1975. Sex pheromone of the moth, Antheraea polyphemus. J. Insect Physiol. 21: 1977-1983.
16. Larsson, M. C. and Svensson, G. P. 2009. Pheromone monitoring of rare and threatened insects: exploiting a pheromone-kairomone system to estimate prey and predator abundance. Conserv. Biol. 23: 1516-1525.
17. Ministère de l'Écologie et du Développement durable (2008) ESPECES ANIMALS. 2008. 1075-Isabelle de France (Graellsia isabellae) Cahiers d'habitats. URL http://www. ecologie. gouv. fr/IMG/natura2000/habitats/pdf/tome7/1075. pdf.
18. Ministerio de Medio Ambiente. 2006. Graellsia isabellae. Catálogo Nacional de Especies Amenazadas. URL http://www.mma.es/secciones/biodiversidad/especies_amenazadas/catalogo_especies/artropodos/pdf/INV38. pdf.
19. 13C NMR chemical shifts of unbranched alk-2-yn-1-ols, 3-alkyn-1-ols and 'internal' alkyn-1-ols. Mag. Res. in Chem. 33: 917-21.
20. Ribe, S., Kondru, R. K., Beratan, D. N., AND Wipf, P. 2000. Optical rotation computation, total synthesis, and stereochemistry assignment of the marine natural product pitiamide A. J. Am. Chem. Soc. 122: 4608-4617.
21. Singh, V., Vig, R., Mohini, V., Trehan, I. R., and Kad, G. L. 1992. Syntheses of (4E, 6E, 11Z)-hexadecatrienyl acetate and (4E, 6E, 11Z)-hexadecatrienal, female sex pheromone of Eri-silkworm, Samia cynthia ricini (Lepidoptera: Saturniidae). Proc. Indian Acad. Sci. (Chem. Sci.) 104: 57-60.
22. Sonnet, P. E. and Heath, R. R. 1980. Stereospecific synthesis of (Z, Z)-11, 13-hexadecadienal, a female sex pheromone of the navel orangeworm, Amyelois transitella (Lepidoptera: Pyralidae). J. Chem. Ecol. 6: 221-228.
23. Tomida, I. and Fuse, T. 1993. Preparation of four geometrical isomers of the Eri-silk moth pheromone, (11Z)-4, 6, 11-hexadecatrienals, and their effect toward male Eri-silk moths. Biosci. Biotech. Biochem. 57: 648-652.
24. Vila, M., Auger-Rozenberg, M. A., Goussard, F., and Lopez-Vaamonde, C. 2009. Effect of non-lethal sampling of DNA on life history traits of the protected moth Graellsia isabelae (Lepidoptera: Saturniidae). Ecol. Entomol. 34: 356-362.
25. Vila, M., Marí-Mena, N., Yen, S.-H., and Lopez-Vaamonde, C. 2010 Characterization of ten polymorphic microsatellite markers for the protected Spanish moon moth Graellsia isabelae (Lepidoptera: Saturniidae). Conserv. Genet. 11: 1151-1154.
26. Witzgall, P., Lindblom, T., Bengtsson, M., and Tóth, M. 2004. The Pherolist. www-pherolist. slu. se.
27. Ylla Ullastre, J. 1997. Història Natural del Lepidòpter Graellsia isabelae (Graells, 1849). Institut d'Estudis Catalans, Arxius de les Seccions de Sciencies CXVI, Barcelona, Spain. 232 p.
28. Zagatti, P. and Malosse, C. 1998. Étude de la phéromone sexuelle et mise au point d'une phéromone de synthèse. (ed. OPIE). In: Contribution à la connaissance de Graellsia isabelae galliaegloria Oberthur (Lepidoptera, Attacidae) connu uniquement en France. Rapport d'études de l'OPIE 3: 26-27.
29. Zeng, X., Zeng, F., Negishi, E.-I. 2004. Efficient and selective synthesis of 6, 7-dehydrostipiamide via Zr-catalyzed asymmetric carboalumination and Pd-catalyzed crosscoupling of organozincs. Org. Lett. 6: 3245-3248.